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7-O-cinnamoyl-5-hydroxygardaloside
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | OCC1O[C@@H](O[C@@H]2OC=C([C@@]3([C@H]2C(=C)[C@H](C3)OC(=O)/C=C/c2ccccc2)O)C=O)C([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C25H28O11/c1-13-16(34-18(28)8-7-14-5-3-2-4-6-14)9-25(32)15(10-26)12-33-23(19(13)25)36-24-22(31)21(30)20(29)17(11-27)35-24/h2-8,10,12,16-17,19-24,27,29-32H,1,9,11H2/b8-7+/t16-,17?,19-,20+,21-,22?,23-,24-,25-/m0/s1 |
| InChIKey | ZDBJIEXNDRVUNP-QQBATWAOSA-N |
| Formula | C25H28O11 |
| HBA | 11 |
| HBD | 5 |
| MW | 504.49 |
| Rotatable Bonds | 7 |
| TPSA | 172.21 |
| LogP | -0.83 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 504.16 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Clerodendrum myricoides | Lamiaceae | Plantae | 54240 |
Showing of synonyms
7-O-cinnamoyl-5-hydroxygardaloside
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)OC(C2=C)CC(C23)C=COC3OC4CCCCO4
Level: 2
Mol. Weight: 504.49 g/mol
SMILES: C1OC=CC(C12)CC(C2=C)OC(=O)C=Cc3ccccc3
Level: 1
Mol. Weight: 504.49 g/mol
SMILES: C=C1CCC(C12)C=COC2OC3CCCCO3
Level: 1
Mol. Weight: 504.49 g/mol
SMILES: C=C1CCC(C12)C=COC2
Level: 0
Mol. Weight: 504.49 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 504.49 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 504.49 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.86
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.8
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.78
- Plasma Protein Binding
- 60.64
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.66
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.32
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.88
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.26
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -595.79
- Rat (Acute)
- 3.83
- Rat (Chronic Oral)
- 3.47
- Fathead Minnow
- 4.15
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 517.48
- Hydration Free Energy
- -3.03
- Log(D) at pH=7.4
- 0.7
- Log(P)
- 0.4
- Log S
- -1.85
- Log(Vapor Pressure)
- -12.07
- Melting Point
- 133.48
- pKa Acid
- 3.78
- pKa Basic
- 2.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8202 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.8126 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8100 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7853 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7673 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7547 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7484 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7479 |
| NAD(P) transhydrogenase subunit alpha part 1 | Q2RSB2 | PNTAA_RHORT | Rhodospirillum rubrum | 3 | 0.7411 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7396 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7359 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7284 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7279 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7264 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7159 |
| Matrix metalloproteinase-20 | O60882 | MMP20_HUMAN | Homo sapiens | 2 | 0.7112 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7041 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7035 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7032 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 2 | 0.7028 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7012 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7007 |